Bush's "yes" or "no" is one of the most significant factors looming over the 2016 Republican presidential contest. A White House bid by the brother and son of presidents would shake up a wide-open GOP field, attract a legion of big-money donors and set up a showdown with the influential tea party movement. Bush has said he'll consult with his family this summer and make a decision by the end of the year.
With New Jersey Gov. Chris Christie facing multiple investigations in a political retribution probe, many Republicans see Bush as a potent alternative: a two-term GOP governor who thrived in the nation's largest swing-voting state and could make the party more inclusive.
Friends and advisers say he is seriously considering a presidential run. His busy schedule will do little to quiet speculation.
This month, Bush is expected to visit New Mexico and Nevada to campaign for Republican governors there, even though both incumbents are widely expected to cruise to re-election. In Las Vegas, he'll address leaders of the Republican Jewish Coalition, an influential political group backed by casino magnate and GOP mega-donor Sheldon Adelson.
And in Dallas next week, Bush is scheduled to co-host an education conference where Clinton is also set to appear.
With no clear frontrunner for the GOP nomination, Bush's standing is rising in early presidential polls and among donors. His popularity with wealthy insiders was on display last month at a Republican fundraiser in the gilded ballroom of Mar-a-Lago, Donald Trump's Palm Beach estate. The night's keynote speaker was a tea party firebrand, Sen. Ted Cruz of Texas, but a short video message from Bush received far more applause.
"Jeb is striking a chord amongst many thoughtful donors," said Fred Malek, finance chairman of the Republican Governors Association.
"He's a proven conservative," Malek said. "But at the same time, he is not viewed as extreme or an ideologue and therefore can appeal to the moderate element of the party as well."
Bush would carry both the benefits and the baggage of one of America's most prominent political dynasties. Its patriarch, George H.W. Bush, was elected to one term in 1988; his son, George W. Bush, served two presidential terms beginning in 2001. The family's vast fundraising network and political connections, in addition to Jeb Bush's own constellation of donors and advisers, could fuel a formidable campaign. A senior adviser at the financial firm Barclays, Jeb Bush remains a favorite of the Wall Street set.
But the shadow of his older brother's controversial presidency still looms. The family's matriarch, former first lady Barbara Bush, has repeatedly spoken of the potential for Bush fatigue, saying, "If we can't find more than two or three families to run for high office, that's silly."
A Washington Post-ABC News poll this month signaled head winds Jeb Bush could face: nearly half of all Americans, and 50 percent of registered voters, said they "definitely would not" vote for him for president.
Nevertheless, friends and advisers say, he is mulling a bid and reaching out to influential donors.
"He is seriously considering this, but he is not following the timeline that the pundits or the press would like him to follow," said Sally Bradshaw, Bush's former chief of staff.
Bush briefly considered a presidential campaign in 2012 but declined to run.
"It's much more serious this time," said Slater Bayliss, a lobbyist and former Bush aide. "The question for him is whether he's willing to make the sacrifices that he's seen his brother and his dad make at a time in his life when he's having an impact on policy issues he cares about."